Winter Date 1, Part 4: Masturbation and Missionary

Caoimhe

“So, I never done this before, obviously.”

Gaia sits on the edge of the bed in the Winter Room, cross-legged, looking at the drow, whose back is resting on the headboard. She has a sleep shirt on, bunched up at her waist, and a cute pair of powder blue panties.

“I don’t think that Andromeda or Tegan did this a bunch before the show either.”

“Did you?”

“During prison, whenever I thought I could get away with it. Before that, I preferred a good dicking down. May I ask why?”

Caoimhe sighs, taking a little solace that Winter texted her permission to think of him as her boyfriend, “The big reason is that Winter is attracted to girls, too. He ate me out a couple of days ago. I know that he is going to want to do more stuff with me like this and I want to be ready for that. Less important, but still needing consideration, this is a part of me now. I spent way too long denying who I was; I shouldn’t do the same to this part of me just because I am a little uncomfortable about it.”

Gaia gives the nervous drow a little smile. That’s sweet. Caoimhe is trying to be a good girlfriend. I’m glad to help.

“So, are you going to get naked for me?”

Caoimhe makes a face at that. “I wasn’t planning on it.”

Gaia shrugs, “I mean, it’s worth points and would help me see what you are doing, but...”

Caoimhe is quick to address it, “Sorry, Gaia, but neither of us needs points that badly and I am already uncomfortable enough with doing this.”

“Okay, I get it,” Gaia says, “You don’t really want to do this with me. We can do this your way. So, I presume you are just interested in using your fingers, right?”

Caoimhe nods. And so, they begin. The drow reaches into her panties and starts to gently rub her folds, starting with the outer ones, then nudging her way across the inner ones. It doesn’t feel like she’s doing much.

“It’s not working,” the frustrated woman cries.

“Hey, did you get instantly hard and cum as a guy? If not, don’t complain. Takes time, especially when you’re not in the mood.”

Caoimhe pouts a little, but nods. She keeps going. A little harder. A little faster. She imagines Winter worshiping her folds with his hand. His tongue lapping at them like before the challenge. She feels herself start to moisten. My cute little sub, looking up at me from between my thighs. Ooh.

Gaia tells her to move her thumb up to where her folds meet up top. She nearly sees stars when she does so. Too much! She pants, slowing down, circling the spot until it doesn’t feel like every nerve ending lighting up like Christmastide lights. When the suggestion comes, she starts to slip a finger inside herself, just to panic at the thought and stop. She focuses on that spot again instead. Circling around it tighter and tighter and tighter until she’s wiggling that nub in a rapid circle.

“FUUUUUUCK!!!!!!!”

Gaia: +1 XP (JOI Instruction for Another Contestant [Kevin])

Kevin: +2 XP (Masturbate for Another Contestant [Gaia])

Kevin: Daily Task Complete! Perform a sex act (with someone new) +10 BP

The drow is left a little boneless, panting and sweaty, on the bed. She pulls her sticky hand out of her panties.

“How you feel, Caoimhe?”

“Well-spent. That what it’s always like, the female orgasm?”

Gaia smirks as she gets up, “Nope. Most of the time, it’s better. See ya later!”

Caoimhe doesn’t try to get up to see Gaia out. She just lets herself fall into reverie.

Ootah

The gym was good. Aunt Josie was understanding and left the orc to her own devices, only coming to spot when Ootah looked like she was doing an especially heavy lift.

Now, back in the Spring Room, her legs feel like jelly. She knows the memes about skipping leg day and, seeing as she will be living on the fourth floor of a tower for the foreseeable future, she can appreciate the temptation. But power from a swing starts with the legs, rotates through the hips and torso, then explodes from the arms. So, if she wants to hit harder, she must suffer those squat lifts.

The shower here is a little nicer than the ones at home. Most of that has to do with proximity to the ocean. Teleptafelya is built on the edge of a mountain, surrounded by high, dry prairie. Water is at a premium and is not used lightly. Here, with the ocean so close and the capital set up with magitech desalination (courtesy of Aunt Mattie), she could stand under the water for hours and not get yelled at.

Ootah admits to herself that some of it is due to the extravagance of the shower’s design. It is of the usual size for an adult (most adults here have shower partners more often than not), but the extra shower heads raining water down is nice. The world where her new Mistress is from has also seemed to have figured out how to liquify soap. This “shampoo” stuff is amazing. Sooo much easier that sudsing up my hair with a bar of soap.

Too soon, she turns off the water and finishes her shower. She dries off and wraps a towel around her head to help avoid tangles as her hair dries. She’ll brush it and braid it for bed soon enough. Ootah does not bother wrapping her body up in another towel once she is dry.

She exits the bathroom, only to see an angry Craig staring her down.

“Evening, Craig. I take too long?” she greets.

“Put some clothes on,” the gnoll snarls. It’s obvious he wants to say more, but bides his tongue.

“I sleep naked, Craig. Get over it.”

“Not with me you don’t.”

“Jealous that my womanhood is much larger than what you are packing?” Ootah moves to the vanity to start preparing her hair for sleep, not bothering to look at her roommate. The gnoll lets out a rumbling growl. He has maybe a couple of inches of height on me, which means his reach is likely a bit longer than mine. He definitely has more weight on me. He carries himself like an accomplished brawler, not a true warrior. If it comes down to blows, I know I can take him. Is it worth taking a punishment?

Hair in a loose braid to minimize tangles in the morning, she turns around to see that Craig is attempting to hog the entirety of the bed. She sighs, “What do you think you’re doing?”

“Getting some shut eye. You can have the couch.”

“The couch? Do I look like someone willing to sleep on the couch? No. Move over.”

“Fuck you!”

Ootah sighs, then gives him a hard look. “You don’t get the power dynamic here, so let me set you straight. I am NOT sleeping on the couch; I am sleeping in the bed. You have a choice. You can either be considerate by moving over or a coward by crawling out of bed to take the couch yourself. Choose.”

Craig makes no effort to move, obviously not understanding. He just repeats, “Fuck you.”

“Fine. If you want to play it this way, let me rephrase. I am ordering your cock to feel like it is in a slowly tightening wine press until you make room for me to get comfortable on the bed.”

The moron laughs, but not for long. They first turn to winces, then whimpers, then bawling his pathetic eyes out, all as she glares at him to comply. He finally rolls to his side. Ootah hears the relief in his voice as she struggles to find the edge of the invisible sheets. As soon as he starts to turn back, thinking his temporary compliance will suffice, Ootah commands again, pointing to a spot on the edge of the mattress, “The tip of your cock is now stuck to this spot right here until you are ready to get out of bed. If you get out of bed, then return before the morning comes, it will feel like bullet ants are stinging your crotch until I willingly and politely say ‘aardvark.’”

He is shifted, pelvis first, into his new position, struggling to get comfortable. Ootah scoots under the sheets and settles in herself. She stares at her reflection in the canopy mirror. Asshole. I shouldn’t need to exploit that transformation to get in bed. Maybe he will learn that I will always outrank him. One can only hope.

Mineko

Mineko carries her homework book upstairs almost as if it is a venomous snake. She hopes that she doesn’t get in trouble for rising above her station. When she arrives, only the other trainer slave is in the Summer Room. She tries her best to hide her book. Tegan, body wrapped up in a towel, notices, “What are you doing?”

I can’t lie! I hope she doesn’t punish me too harshly! “Ahh, hiding a book?”

The kitsune looks at her as if that is an odd thing to do instead of a deeply inappropriate one. She steps closer, asking, “Why are you hiding a book? Is it perverted?”

“Slaves aren’t supposed to have books. But the trainer slave Tessa told me to learn to read, so...”

Mineko anticipates Tegan’s anger. She got it, but not the kind she expected. “What do you mean, you don’t know how to read? The fuck is wrong with...”

Gaia walks in and gives Mineko some immediate pets. Feels good! She purrs contentedly. By the time the pets are done, trainer slave Tegan is much less angry.

“Tell me everything you don’t know how to do that I think you should,” the kitsune commands.

Mineko cocks her head to the side. She looks to Gaia, asking, “How do I answer that question? I don’t know what the trainer slave expects me to know.”

Tegan bristles at her title. Gaia asks Mineko to go get ready for bed. She curtsies then heads to the bathroom. Strip down to only wearing her collar. Lick her forepaws clean. Curl up to lick her hindpaws clean too. Brush her tails and her hair. Clean her teeth.

When she returns ready for bed, phone notifications go off.

Gaia: Daily Task Complete! Play the Pet with Mistress and Show Off Your Collar +20 BP

Mineko: Daily Task Complete! Play the Pet with Mistress and Show Off Your Collar +20 BP

Mineko: +4 XP (Full Frontal Nudity for Another Contestant [Gaia, Tegan])

“Why are you naked?” Tegan asks, sounding like she is trying to avoid conveying her obvious irritation.

Again, the kitsune is confusing. “I was ordered to get ready for bed? I am ready for bed.”

Gaia asks, “Do you have sleep clothes, Mineko?”

The confusion deepens. “Sleep clothes? What are sleep clothes?”

Tegan crawls into bed, still not properly naked. Gaia shrugs and heads to the bathroom returning naked, as is right and proper for bed. Tegan groans, “Not you, too! Why is everyone a pervert?”

Gaia: +1 XP (Show Bare Crotch for Another Contestant [Mineko])

Gaia gets in the middle, then Mineko snuggles in beside her. “What does pervert mean? Training slave Tegan seems to use that word a lot.”

Gaia helpfully switches to Sylvan, “[You know, pervert?]”

Mineko rests her head on Gaia’s breast. “[I do not know that word in Sylvan either.]”

Gaia rubs the small of Mineko’s back as she replies, “It’s okay. Not an important word anyways. Want to practice reading your book until you are ready for bed?”

Nodding, Gaia has the three of them sit up. The one-tailed cat girl opens the book and Mineko tries her best to read it. While trainer slave Tegan looks frustrated, Gaia is patient and gentle. Mineko likes Gaia; she wants all her relationships with her fellow slaves to be this good.

Soon, she is too tired to keep her eyes open. She feels herself lowered onto her side as Gaia wraps her arms around her. She thinks about the day. Having actual fish instead of gruel. Buying clothes like she is a person. Learning to read a little like she is a person. Does Owner-Mona truly want her as more than a slave? Maybe she will find out for sure tomorrow...

Mona

As soon as Winter enters the bedroom, he shunts his clothes into his inventory. Mona gets a good, hard look at his new and improved backside. Where he looked soft with Kevin, he looks fuller. He’s not bulky or a beefcake by any stretch of the imagination, but he does have muscle definition. Something is sparkling between his butt cheeks, which is very interesting. His back flexes as he turns to look at her, snarking, “You like, Mistress?”

Mona nods excitedly.

“Good. Don’t just stand there. Come get a good feel.”

The gamer girl does not need more of an invitation. She wraps Winter in her arms from behind. Winter strokes her behind her ear for a few moments, then coughs.

“Oh, sorry.”

“No worries, Mistress. But we do have some things to discuss first. If you will do me the kindness of having a seat on the bed.”

Mona sits, starting to undress, only for Winter to gently hold her hands still. He is hard and throbbing, which distracts the Mistress. He is sooooo cute!

Winter: +4 XP (Full Frontal Nudity for Mistress)

“I will handle that in a moment, Mistress.”

Mona smiles, asking, “Is that a submissive thing, undressing your Mistress?”

“Well, yeah, but it’s also worth points.”

Mona arches an eyebrow. “Wait, do you know everything about the points system in the game?”

“Only what the others have done, at least until yesterday. That’s beside the point. We need to talk about what is about to happen.”

Mona looks into Winter’s eyes. There is no fear or trepidation there. Just anticipation and a little touch of hope? What is he hoping for?

Things make a lot more sense when he lets go of her wrists. He pulls objects out of his inventory. First, a bottle of lube, which he tosses to Mona. She awkwardly catches it; then he says, “We’ll need that either way. Wait until you decide before starting to use it.”

“Why? It has aphrodisiacs in it or something?”

“More like you don’t know where to put it yet,” he snarks, then each of his hands has inventory items in it. One hand has a condom, the other a dildo harness with a smallish dildo already attached. He continues, a little more seriously, “So, you have options, Mistress. The one I expected you to already be thinking of is pegging me. If that is what you want to do tonight, that is fine. I will enjoy it immensely and I am sure you will like it too. But, there is another possibility I want you to consider.”

His eyes look down and Mona starts to understand. He is hard down there, a little bead of pre-cum forming on his tip. Cute! He’s twitching from me looking at him!

“Your first time was done wrong, Mistress. I am large for an elf, but still small by human standards. While I know my cousin will be as gentle as she can be in a couple of days, I would be quite happy to try my new equipment out if you’d like to try taking someone more... manageable inside you.”

Mona looks from one of Winter’s hand to the other. Frankly, she is torn. The idea of pegging a cute boy is quite a turn on; the idea of getting some practice with a real cock before facing Ootah’s 16 inch monster is quite enticing. She asks, “Can we do both?”

“You think you can handle two rounds of intense lovemaking right now, my Mistress?” Winter responds with a smirk, “You haven’t yet. And you got a transformation that may make it harder for you to continue past the first round...”

Oh, right. Delayed Gratification, Accelerated did promise that sex will feel better. Maybe I should get, I don’t know, a sex stamina boost? Still... “I want to do both. You are probably right that I can’t do both not tonight, but...”

Winter leans in to plant a kiss on Mona’s lips. His makeup smudges a little. “To spoil a surprise, Kevin and I are planning on a threesome with you on his date. My ass will be stuffed that night for sure. You can negotiate with him to have a turn back there.”

Mona stares into his eyes again. He really wants to fuck me like a boy right now, doesn’t he? She snatches the condom from his hand and opens the package. She does not need her transformation to see the excitement in his eyes.

“Uh, how do I put this on you?”

He guides her through the process. She checks that it is rolled the right way, then applies a tiny little drop of lube inside the reservoir. He teases her as she unfurls the condom along his “massive three inches of drow sex stalactite.” Soon enough, he’s wrapped up.

Winter: +8 XP (Mistress Applied a Condom to Contestant, x4 bonus [first time both participants])

“Okay, that wasn’t too bad. Curious as to why you brought some?”

Winter explains as he lovingly undresses her. Between little kisses along recently exposed skin, he murmurs, “I figured better safe than sorry. Statistically, someone is going to be pregnant by the end of the game, likely multiple someones. While you can use transformations to control whether that happens to you with Ootah and Craig, I could knock you up. Until you are ready to have cute little drow babies with me, I will wrap it up.”

Winter: +2 XP (Undress the Mistress)

Winter: +8 XP (See Mistress Naked)

“Wow. Thank you. I didn’t even think about that... You really want kids with me?”

Winter shrugs as he helps lay Mona down. “I know that I will want kids with my Mistress eventually. Not NOW, but once we have a well established rapport. How do you want me to serve you tonight?”

“Something easy?”

Winter nods, then helps Mona get comfortable laying on her back, fluffing up a couple of pillows to elevate her head. He spreads her legs apart, then positions himself between them. Warming the lube in his hands, he applies it to the wrapped wang, then to Mona’s external bits. Finally, each foot gets to rest on one of Winter’s shoulders. Angling his lower head towards her lower lips, he asks, “Comfy? Ready?”

Mona nods. Winter pushes in. The sensation is very different than Craig. It’s not just that Winter bottoms out before he hits her womb, though that is different (and appreciated). Winter is savoring the feeling; he takes his time, going at a pace that is a little slow.

“I’m not that fragile, Winter.”

“Sorry, Mistress. Even though the condom, it feels so good to be inside you.”

Mona laughs, then commands in her best Mistress voice, “Well, pick up the pace!”

“Yes, ma’am!” Winter quips, in his most subservient tone. It is somewhat undermined by his sarcastic salute. The pace picks up. He angles himself to kiss her fluttering walls such that that special place inside is nearly continuously caressed. Mona finds herself wrapping her legs around his neck; he plows through. The pace he sets keeps ramping up. She starts seeing stars.

“This adequate, Mistress?”

Mona can barely understand words right now. She babbles out happily instead. Winter keeps up the pace, thrusting and pressing himself into that perfect spot.

The first orgasm hits like a freight train. Mona doesn’t know if it was the bonus pleasure from the transformation or Winter’s natural skill or both. She doesn’t know much of anything right now. Her walls clench tightly around the pistoning prick, desperate to hold onto it forever. He keeps going, elongating the sensation. It feels like she keeps cumming, over and over. By the time she comes down, he pops out, collapsing down into her embrace, panting. She, boneless, can barely bring herself to hold onto him.

Winter: +20 XP (Vaginal Sex with Mistress [x2 bonus, first time contestant participant])

Winter: Daily Task Complete! Sex Act with New Person +10 BP

“Worth it, Mistress?” Winter pants out into her bare breast.

“Worth it,” she happily slurs.

He is slow to rise, but, reluctantly, does so. He checks that the condom held (it did!), then proceeds to remove it and tie it off. “Wanna souvenir?”

Mona laughs, despite being breathless, “Really?”

Too tired to get up, yet too sweaty feeling to get comfortable for bed, Mona casts Prestidigitation several times to clean both of them. The effort seems to be appreciated by her subby little drow. Now completely spent, she is feeling really groggy.

“Does Mistress wish to be the little spoon tonight?”

Mona murmurs her consent. Happily, Winter understands. She feels her back pulled into his chest. His softening erection lines up just above her butt cheeks. She snuggles into him and begins to fall asleep.

Winter: +1 XP (Spoon the Mistress)